1. Field of the Invention
The present invention relates to compositions of matter classified in the art of chemistry as bis-[4-(R-amino)-1-pyridinium]alkanes, to a process for the preparation thereof, to compositions containing these compounds and to methods of using the same for controlling microorganisms and for preventing the formation of dental plaque.
2. Prior Art
Walker U.S. Pat. No. 3,055,902, issued Sept. 25, 1962 discloses a group of bis-(4-amino-1-pyridinium)alkanes. No utility is disclosed for these compounds other than as intermediates in the preparation of the corresponding bis-(4-amino-1-piperidino)alkanes which are stated to have bacteriostatic and bactericidal effects.
G. N. Walker et al., J. Org. Chem. 26, 2740-7 (1961) disclose essentially the subject matter disclosed in the above-noted Walker U.S. patent.
W. C. Austin et al., J. Pharm. Pharmacol. 11, 80-93 (1959) disclose 1,10-bis-(4-amino-1-pyridinium)decane diiodide and 1,10-bis(4-acetamido-1-pyridinium)decane diiodide. It is stated that certain species among the large, diverse group of quaternary ammonium compounds disclosed possess amebicidal, antibacterial, anti-filarial and trypanocidal activity, but no biological data are given for either of the above-named compounds.
Edwards U.S. Pat. No. 3,786,058, issued Jan. 15, 1974 discloses a group of bis(pyridinium quaternary salts) believed to be structurally more remote from the claimed compounds than the above-noted Walker and Austin et al. compounds and having the formula ##STR1## wherein inter alia: R.sub.1 and R.sub.2 are alkyl of 6 to 14 carbon atoms;
A.sub.1 and A.sub.2 are a direct linkage; PA1 A.sub.3 is --NH(CH.sub.2).sub.m NH--, m being 0 to 12; and PA1 X.sup.1.X.sup.2 represents two monoanions or a dianion. It is stated that the compounds possess antibacterial properties and that some are useful in dental hygiene for inhibiting the formation of dental plaque. In the above compounds the pyridinium groups are linked through an alkylene diamine chain bonded to the carbon atoms of the pyridine rings and thus constitute a class of compounds which are separate and distinct from the instantly claimed bis-(pyridinium)alkanes in which the pyridinium groups are linked through an alkylene group bonded to the nitrogen atoms of the pyridine rings. PA1 R is an alkyl group containing from 6 to 18 carbon atoms, a cycloalkyl group containing from 5 to 7 carbon atoms, benzyl, or phenyl substituted by methylenedioxy or one or two substituents selected from the group consisting of halogen, lower-alkyl, lower-alkoxy, nitro, cyano and trifluoromethyl; PA1 R.sub.1 is hydrogen or lower alkyl; PA1 A is an anion; PA1 m is 1 or 3; PA1 n is 1 or 2; PA1 x is 1, 2 or 3; and